Combining the catalytic enantioselective reaction of visible-light-generated radicals with a by-product utilization system
Webster, Richard David
Date of Issue2017
School of Physical and Mathematical Sciences
We report an unusual reaction design in which a chiral bis-cyclometalated rhodium(III) complex enables the stereocontrolled chemistry of photo-generated carbon-centered radicals and at the same time catalyzes an enantioselective sulfonyl radical addition to an alkene. Specifically, employing inexpensive and readily available Hantzsch esters as the photoredox mediator, Rh-coordinated prochiral radicals generated by a selective photoinduced single electron reduction are trapped by allyl sulfones in a highly stereocontrolled fashion, providing radical allylation products with up to 97% ee. The hereby formed fragmented sulfonyl radicals are utilized via an enantioselective radical addition to form chiral sulfones, which minimizes waste generation.
© 2017 The Author(s) (published by Royal Society of Chemistry). This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.